The Outfit Read Free

west bank. And nowhere was this obvious rags-to-riches path more adroitly perceived than in America’s “second city.” Named for the Ojibwa Indian word for the foul-smelling, river-clogging “wild onion”
(checagou),
it had already elevated political corruption to an art form. Chicago, the future home of The Outfit, embraced prohibition with open arms.
    “That Toddlin’ Town"
    Geography and geology play pivotal roles in the character of any city. Chicago’s placement on the map dictated that eastern urbanity come face-to- face with the take-the-law-into-your-own-hands mentality of the recently opened Wild West. After its incorporation in 1837, Chicago became the gateway to this new frontier and as such was guaranteed a steady stream of tourist business. Literally hundreds of wagons, overflowing with anxious homesteaders, transited Chicago every day. 1
    Chicago soon amassed a glut of discretionary money, its coffers bulging with profits from manufacturing, commodities auctions, and huge stockyards that “rendered” seventeen million head of Western cattle a year. The party was on, and with the swiftness of a barroom pickpocket, Chicago became transformed into “That Toddlin’ Town.” Hotels and saloons were jammed with a mostly male clientele who had set out from the East in advance of the womenfolk. And these adventurers saw Chicago as their last chance for a little TLC before their trek into the harsh Western frontier. What transpired next was inevitable: Where there are unsupervised males there are saloons; where there are saloons, there are gambling and girls. The gamblers’ haunts acquired their own colorful nicknames, such as Hair-Trigger Block, Thieves Corner, and Gambler’s Row.
    Not far behind the saloon owners came the con men and swindlers. On some occasions, the con men
were
the saloon owners. One such character was Mickey Finn, who operated two establishments on Whiskey Row. Finn’s now infamous concoction, The Mickey Finn Special, was a drink tainted with a secret powder that rendered the drinker unconscious. While touring the twilight zone, the unfortunate reveler had his pockets emptied by the unscrupulous Finn. As they had throughout time, the criminal element found refuge in a district that seemed to be earmarked just for them. And it was one of the most bizarre vice districts imaginable.
    The Underworld
    If the good citizens of Chicago desired a law-abiding community in which to plant roots, geology conspired with geography to stack the cards in defiant opposition. For although Chicago
seemed
to be the right place to erect a city, nature had other ideas. The city, it turned out, was built on a smelly swamp/marsh, which was a sort of primordial soup for the gangster empires of the future. By the late 1850s, torrents of mud threatened to engulf the town, which had no paved streets. Cracks in the wooden slabs that functioned as thoroughfares oozed the muck around the wheels of carriages and the shins of well-dressed ladies. Mud Town and Slab Town were added to the list of unflattering nicknames for Chicago.
    The city fathers concocted an ingenious, if optimistic, solution to the muddy onslaught: jack up the entire city ten feet while fortifying the surface with stone. Given that the buildings themselves were constructed from relatively light wood, the idea was deemed feasible. Thus, for ten years Chicago existed on stilts, creating a cavernous “underworld,” as it came to be known. Soon, the underworld gave shelter to a repellent assemblage of humanity loosely commanded by Chicago’s first criminal-empire czar, Roger Plant.
    An immigrant boxer from England, Plant built a two-story paean to perversity called Under the Willows. The first floor consisted of round-the- clock boozing and gambling; the second tier was the domain of more than two hundred prostitutes, whose window shades were lettered on the outside with the slogan Why Not?
    As unsavory as the Willows was, it paled in comparison to